Preorganization-enhanced halogen bonding via intramolecular hydrogen bonding: a theoretical study
- PDF / 1,615,467 Bytes
- 11 Pages / 595.276 x 790.866 pts Page_size
- 88 Downloads / 145 Views
ORIGINAL RESEARCH
Preorganization-enhanced halogen bonding via intramolecular hydrogen bonding: a theoretical study Yanling Huang 1 & Shaoze Zhang 2 & Zhijian Xu 3 & Honglai Liu 1 & Yunxiang Lu 1 Received: 5 March 2020 / Accepted: 11 May 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Cationic and neutral halogen bonding (XB) donors use two types (I and II) of intramolecular hydrogen bonding (HB) to preorganize structures and increase the efficiency of halide anion recognition. Herein, several XB donors with and without preorganization function were studied. The amine group was introduced to form type I intramolecular HBs (inside of the binding site) for cationic XB donors, and the hydroxyl group was employed to provide type II intramolecular HBs (outside of the binding site) for neutral XB donors. From energetic prospective, the complexation between the receptors and halide anions was enhanced with the preorganization function, which is mainly contributed by the improved coplanarity of the donor geometries. The type II intramolecular HBs are predicted to be much stronger than the type I intramolecular HBs, and the coplanarity of the preorganization structures including type II intramolecular HBs would be further improved with the binding of halide anions. We hope that the results reported herein will assist in the application of preorganization in anion recognition process. Keywords Intramolecular hydrogen bonding . Halogen bonding . Anion binding . Preorganization
Introduction Preorganization, a central determinant of binding power, assists precise hosts-guests organization and complexation from both enthalpic and entropic perspectives [1–3]. Owing to high degrees of preorganization, the biological systems, such as the enzymes, the genes, and the antibodies, could accomplish intricate responsibilities [4–6]. In general, their functional groups act cooperatively as binding sites which are principally Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11224-020-01559-z) contains supplementary material, which is available to authorized users. * Shaoze Zhang [email protected] * Yunxiang Lu [email protected] 1
Key Laboratory for Advanced Materials and Department of Chemistry, East China University of Science and Technology, Shanghai 200237, China
2
National Engineering Laboratory for Vacuum Metallurgy, Kunming University of Science and Technology, Kunming 650093, China
3
Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
oriented prior to complexation. Thus, developing new organization methods or highly structured complexes and revealing the nature that governs their behaviors are valuable to many fields influenced by supramolecular chemistry. Preorganization processes in biomolecular and supramolecular structures rely on diverse noncovalent interactions, such as hydrogen bonding (HB) [7–12], ion-paring interactions [13–15], and π-π stacking [16–19]. Intramolecu
Data Loading...
